Aromatic amine derivative, and organic electroluminescent element containing same

Patent metadata

Field	Value
Publication number	US-9837616-B2
Application number	US-201214233370-A
Country	US
Kind code	B2
Filing date	Jul 23, 2012
Priority date	Jul 26, 2011
Publication date	Dec 5, 2017
Grant date	Dec 5, 2017

Abstract

An aromatic amine derivative represented by the following formula (1): wherein
Z 1 is a group represented by the following formula (2); Z 2 is a group represented by the following formula (3) or (3′); and P and Q are independently a group represented by the following formula (4) or (5):

First claim

The invention claimed is:

1. An aromatic amine derivative represented by the following formula (1):
[Z 1 n L 1   (1)

wherein Z 1 is a group represented by the following formula (2);
L 1 is a group represented by any of the following formulas:

n is an integer of 2 to 10:
[Z 2 m L 2   (2)

wherein Z 2 is a group represented by the following formula (3) or (3′);
L 2 is a group represented by the following formula:

wherein R 5 , R 6 , R 7 and R g are independently a hydrogen atom, a liner or branched alkyl group including 1 to 20 carbon atoms, a liner or branched alkenyl group including 2 to 20 carbon atoms, a cycloalkyl group including 3 to 20 carbon atoms, a trialkylsilyl group including an alkyl group including 1 to 20 carbon atoms, a triarylsilyl group including an aryl group including 6 to 24 ring carbon atoms, an alkylarylsilyl group including an alkyl group including 1 to 20 carbon atoms and an aryl group including 6 to 24 ring carbon atoms, an aryl group including 6 to 24 ring carbon atoms or a heteroaryl group including 5 to 24 ring atoms;
R 5 and R 6 and/or R 7 and R 8 may be bonded to each other to form a saturated or unsaturated ring;
x and y are an integer of 1≦x≦3 and an integer of 1≦y≦3, respectively, and when x is 2 or 3, each R 7 may be the same or different, and when y is 2 or 3, each R 8 may be the same or different;
L 1 in the formula (1) bonds to any of Z 2 and L 2 ; and
m is an integer of 2 to 10:

wherein in the formulas (3) and (3′),
A is a hydrogen atom, a substituted or unsubstituted aromatic hydrocarbon group including 6 to 25 ring carbon atoms, a substituted or unsubstituted aromatic heterocyclic group including 5 to 25 ring atoms or a group formed of plural rings;
A′ is a single bond, a substituted or unsubstituted aromatic hydrocarbon group including 6 to 25 ring carbon atoms, a substituted or unsubstituted aromatic heterocyclic group including 5 to 25 ring atoms or a group formed of plural rings;
B is a single bond, a substituted or unsubstituted aromatic hydrocarbon group including 6 to 25 ring carbon atoms, a substituted or unsubstituted aromatic heterocyclic group including 5 to 25 ring atoms or a group formed of plural rings;
C is a single bond, a substituted or unsubstituted aromatic hydrocarbon group including 6 to 25 ring carbon atoms, a substituted or unsubstituted aromatic heterocyclic group including 5 to 25 ring atoms or a group formed of plural rings;
P and Q are independently a substituted or unsubstituted aromatic hydrocarbon group including 6 to 25 ring carbon atoms, a substituted or unsubstituted aromatic heterocyclic group including 5 to 25 ring atoms, a group formed of plural rings or a group represented by the following formula (4) or (5);
when Z 2 is represented by the formula (3), L 2 bonds to any of A, B, C, P and Q, and when Z 2 is represented by the formula (3′), L 2 bonds to A′; and
k and 1 are independently an integer of 0 or 1, and k+1≧1:

wherein in the formula (4), X is —O—, —S—, or —N(R a )—, R a is an atom or a group selected from a hydrogen atom, a substituted or unsubstituted linear or branched alkyl group including 1 to 20 carbon atoms, a substituted or unsubstituted linear or branched alkenyl group including 2 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group including 3 to 20 carbon atoms, a trialkylsilyl group of which the alkyl parts are each a substituted or unsubstituted alkyl group including 1 to 20 carbon atoms, a triarylsilyl group of which the aryl parts are each a substituted or unsubstituted aryl group including 6 to 24 ring carbon atoms, an alkylarylsilyl group including a substituted or unsubstituted alkyl group including 1 to 20 carbon atoms and a substituted or unsubstituted aryl group including 6 to 24 ring carbon atoms, a substituted or unsubstituted aryl group including 6 to 25 ring carbon atoms and a substituted or unsubstituted heteroaryl group including 5 to 24 ring atoms;
R 1 and R 2 are independently an atom or a group selected from a substituted or unsubstituted linear or branched alkyl group including 1 to 20 carbon atoms, a substituted or unsubstituted linear or branched alkenyl group including 2 to 15 carbon atoms, a substituted or unsubstituted cycloalkyl group including 3 to 20 carbon atoms, a trialkylsilyl group of which the alkyl parts are each a substituted or unsubstituted alkyl group including 1 to 20 carbon atoms, a triarylsilyl group of which the aryl parts are each a substituted or unsubstituted aryl group including 6 to 24 ring carbon atoms, an alkylarylsilyl group including a substituted or unsubstituted alkyl group including 1 to 20 carbon atoms and a substituted or unsubstituted aryl group including 6 to 24 ring carbon atoms, a substituted or unsubstituted aryl group including 6 to 24 ring carbon atoms, a substituted or unsubstituted heteroaryl group including 5 to 24 ring atoms, a halogen atom and a cyano group, and adjacent R 1 groups, adjacent R 2 groups, and/or adjacent R 1 and R 2 may bond to each other to form a saturated or unsaturated ring;
a and b are independently an integer of 0 to 3 and
Q 1 and Q2 are independently a group including 5 to 25 atoms which forms a saturated or unsaturated ring;
in the formula (5), Ar 1 and Ar 2 are independently a substituted or unsubstituted aromatic hydrocarbon group including 6 to 25 ring carbon atoms or a substituted or unsubstituted aromatic heterocyclic group including 5 to 25 ring atoms, and at least one of Ar 1 and Ar 2 is a group formed of plural rings including 9 to 40 ring carbon atoms or a fused aromatic ring group including 10 to 25 ring carbon atoms.

2. The aromatic amine derivative according to claim 1 , wherein one or more selected from A and A′ is a linkage group or a group comprising a group represented by any of the following formulas:

wherein R 3 and R 4 are independently a hydrogen atom, a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group or a t-butyl group;
j is an integer of 2≦j≦20, each R 3 may be the same or different, and each R 4 may be the same or different:

wherein R 5 , R 6 , R 7 and R 8 are independently a hydrogen atom, a liner or branched alkyl group including 1 to 20 carbon atoms, a liner or branched alkenyl group including 2 to 20 carbon atoms, a cycloalkyl group including 3 to 20 carbon atoms, a trialkylsilyl group including an alkyl group including 1 to 20 carbon atoms, a triarylsilyl group including an aryl group including 6 to 24 ring carbon atoms, an alkylarylsilyl group including an alkyl group including 1 to 20 carbon atoms and an aryl group including 6 to 24 ring carbon atoms, an aryl group including 6 to 24 ring carbon atoms or a heteroaryl group including 5 to 24 ring atoms;
R 5 and R 6 and/or R 7 and R 8 may be bonded to each other to form a saturated or unsaturated ring;
x and

Assignees

• Shiomi Takushi
• Watanabe Masami
• Eida Mitsuru
• Idemitsu Kosan Co

Inventors

• Shiomi Takushi
• Watanabe Masami
• Eida Mitsuru

Classifications

• C08G61/12

  Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule · CPC title

• H01L51/5012

  Electricity · mapped topic

• C08G61/124

  with a five-membered ring containing one nitrogen atom in the ring · CPC title

• H01L51/0059

  Electricity · mapped topic

• C08G2261/124

  alternating · CPC title